2-[(4aS,5S,6S,8aS)-6-(methoxymethoxy)-2,2,5,6-tetramethyl-4a,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-5-yl]ethanol | 959470-19-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(4aS,5S,6S,8aS)-6-(methoxymethoxy)-2,2,5,6-tetramethyl-4a,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-5-yl]ethanol
• CAS: 959470-19-0
• 化学式: C₁₆H₃₀O₅
• 分子量: 302.411
• InChiKey: BUXSVGKCZRIIQK-SDADXPQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(4aS,5S,6S,8aS)-6-(methoxymethoxy)-2,2,5,6-tetramethyl-4a,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-5-yl]ethanol 在 吡啶 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以95%的产率得到2-[(4aS,5S,6S,8aS)-6-(methoxymethoxy)-2,2,5,6-tetramethyl-4a,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-5-yl]acetaldehyde
  参考文献：
  名称：

  A Domino-Based Approach toward Stereodefined Heavily Functionalized Cyclohexanes:  Synthesis of Iridal's Core Structure

  摘要：

  A stereoselective synthesis of heavily functionalized six-membered ring subunits, which possess functionality at sites appropriate for further elaboration, is described. The cyclopentanone moiety of hydrindenediol is required to achieve total facial selectivity during the pre-domino installation of the second quaternary center, while oxidative cleavage is responsible for the ring-expanding rearrangement. A microwave-assisted version of the key domino transformation and a test of concept approach toward the iridal core structure are also presented.

  DOI：

  10.1021/ol702056s
• 作为产物：
  描述：

  [(1R,3R,6S,7S,8S,9S)-3-acetyloxy-6-(methoxymethoxy)-6,7-dimethyl-2,10-dioxatricyclo[5.3.1.03,8]undecan-9-yl] acetate 、 丙酮 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 2-[(4aS,5S,6S,8aS)-6-(methoxymethoxy)-2,2,5,6-tetramethyl-4a,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-5-yl]ethanol
  参考文献：
  名称：

  Enantioselective Synthesis of Iridal, the Parent Molecule of the Iridal Triterpenoid Class

  摘要：

  The monocyclic triterpene iridal 1 (parent molecule) is synthesized by an approach that allows access for several representatives of the iridal family as well as diversely substituted analogues. The success of the proposed synthetic plan depends upon. the effortless stereoselective establishment of the trans C10/C11 dimethyl relationship in B-ring moiety 7 using a domino-based methodology and the higly efficient Miyaura - Suzuki type sp(3) - sp(2) segment coupling 7 and 8, respectively.

  DOI：

  10.1021/ol8005425

文献信息

• A Domino-Based Approach toward Stereodefined Heavily Functionalized Cyclohexanes:  Synthesis of Iridal's Core Structure
  作者：Andrei Corbu、Guillaume Gauron、Juan M. Castro、Mohamed Dakir、Siméon Arseniyadis

  DOI：10.1021/ol702056s

  日期：2007.11.1

  A stereoselective synthesis of heavily functionalized six-membered ring subunits, which possess functionality at sites appropriate for further elaboration, is described. The cyclopentanone moiety of hydrindenediol is required to achieve total facial selectivity during the pre-domino installation of the second quaternary center, while oxidative cleavage is responsible for the ring-expanding rearrangement. A microwave-assisted version of the key domino transformation and a test of concept approach toward the iridal core structure are also presented.
• Enantioselective Synthesis of Iridal, the Parent Molecule of the Iridal Triterpenoid Class
  作者：Andrei Corbu、Maurizio Aquino、T. V. Pratap、Pascal Retailleau、Siméon Arseniyadis

  DOI：10.1021/ol8005425

  日期：2008.5.1

  The monocyclic triterpene iridal 1 (parent molecule) is synthesized by an approach that allows access for several representatives of the iridal family as well as diversely substituted analogues. The success of the proposed synthetic plan depends upon. the effortless stereoselective establishment of the trans C10/C11 dimethyl relationship in B-ring moiety 7 using a domino-based methodology and the higly efficient Miyaura - Suzuki type sp(3) - sp(2) segment coupling 7 and 8, respectively.